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Synlett 2012; 23(5): 801-804
DOI: 10.1055/s-0031-1290302
DOI: 10.1055/s-0031-1290302
letter
Copper-Catalyzed Aerobic Oxidative Synthesis of Primary Amides from (Aryl)methanamines
Further Information
Publication History
Received: 08 December 2011
Accepted after revision: 08 January 2012
Publication Date:
27 February 2012 (online)
Abstract
A copper-catalyzed aerobic oxidative method for the synthesis of primary aryl amides has been developed, and the direct oxygenation of (aryl)methanamines to primary aryl amides by molecular oxygen showed convenient, practical, and environment-friendly advantages. This method will find wide application in chemistry and biology.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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- 16 General Procedure for the Synthesis of Compounds 2a–l A 25 mL Schlenk tube was charged with a magnetic stirrer, (aryl)methanamine (1, 0.5 mmol), K2CO3 (1 mmol, 138 mg), and CuBr (0.1 mmol, 14 mg) in mixed solvent of DMSO (2 mL) and H2O (40 μL). The mixture was allowed to stir under O2 (1 atm) at 140–160 °C for 6–12 h (see Table 2 for details). After completion of the reaction, the resulting solution was cooled to r.t. and filtered, and the solvent of filtrate was removed with the aid of a rotary evaporator. The residue was purified by column chromatography on silica gel using PE–EtOAc as eluent to provide the desired product 2. Analytical Data for Two Typical Examples 3-Pyridinecarboxamide (2i) 17 Eluent: EtOAc; yield 55 mg (90%); white solid; mp 131–132 °C (lit.17 131–132 °C). 1H NMR (300 MHz, DMSO-d 6): δ = 9.09 (s, 1 H), 8.74 (d, 1 H, J = 4.1 Hz), 8.26 (d, 2 H, J = 8.3 Hz), 7.68 (s, 1 H), 7.53 (dd, 1 H, J = 4.8, 4.8 Hz). 13C NMR (75 MHz, DMSO-d 6): δ = 166.5, 151.9, 148.7, 135.3, 129.7, 123.5. ESI-MS: m/z = 123.4 [M + H]+. 2-Furancarboxamide (2k) 17 Eluent: PE–EtOAc (1:1); yield 42 mg (76%); white solid; mp 140–142 °C (lit.17 140–142 °C). 1H NMR (300 MHz, DMSO-d 6): δ = 7.81 (s, 1 H), 7.76 (s, 1 H), 7.37 (s, 1 H), 7.10 (d, 1 H, J = 3.4 Hz), 6.60 (dd, 1 H, J = 1.7, 1.7 Hz). 13C NMR (75 MHz, DMSO-d 6): δ = 159.4, 148.0, 145.0, 113.6, 111.8. ESI-MS: m/z = 112.5 [M + H]+
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